


I Like Who I Am, Do You?

by mattzerella_sticks



Series: Season 14 Inspired [20]
Category: Supernatural
Genre: Angst and Humor and Feels and Fluff, Bisexual Dean Winchester, Canon Compliant, Castiel and Dean Winchester Have a Profound Bond, Castiel and Dean Winchester and Sam Winchester are Jack Kline's Parents, Castiel and Dean Winchester in Love, DCVDay, Dean Winchester Comes Out, Dean Winchester In Love, Dean Winchester is Jack Kline's Parent, Dean is more comfortable with who he is, Domestic Fluff, Embarrassed Dean Winchester, F/M, Family Bonding, Father-Son Relationship, John Winchester's A+ Parenting, John was a bad guy the Winchesters know this but they still love him, Love Confessions, M/M, Mother-Son Relationship, Moving On, Nervous Dean Winchester, Openly Bisexual Dean Winchester, Pizza, Post-Episode: s14e13 Lebanon, Proud Dean Winchester, References to Canon, Sappy, Self-Acceptance, Self-Love, Supportive Dean Winchester, Supportive Mary Winchester, Supportive Sam Winchester, Sweet Castiel/Dean Winchester, Sweet Dean Winchester, The Bunker's kitchen, Valentine's Day, ariana grande - Freeform, yet they also won't let his ghost dictate how they should act and live their lives
Language: English
Status: Completed
Published: 2019-02-14
Updated: 2019-02-14
Packaged: 2019-10-28 12:48:52
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 13,151
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17787704
Author URL: https://archiveofourown.org/users/mattzerella_sticks/pseuds/mattzerella_sticks
Summary: Nearly a month after the events of "Lebanon", Dean has slowly but steadily been tearing down his walls. It's one thing to say he liked who he was, and another to live it. He's getting there, one day at a time. But with Valentine's Day around the corner, Dean wants to take his largest step yet by asking Cas out on a date.With help from his family, can he do it? And will Cas say yes? Dean has a good feeling, but it's always a toss-up for a Winchester whenever the forecast calls for happiness.Because Dean might like who he is, that doesn't mean Cas will. That's what makes it all the more nerve-wracking for him.Happy Valentine's Day #DCVDay





	1. Sam

**Author's Note:**

> Finally posting this!! I have been mulling over this FOR DAYS - going from it being a one-shot to a multi-chapter fic, seeing posts about meta that had me re-thinking different ways to go about this. I was going nuts staring at my Word Document.
> 
> ALL so I could get this posted on Valentine's Day! And now that it's here, please enjoy!!

            Dean poured more sauce into the pan, pointedly ignoring the calendar hanging across the room. It had greeted Dean upon entry with blaring red circles over one of its many boxes. They weren’t there last he checked, so before doing anything else he stepped closer to investigate. What he found made his face burn the same bright color of the marker used. After that he forced his eyes away, always stopping himself before the calendar reached his line of sight again. It hadn’t helped that throughout the entirety of his time in the kitchen it sang a distracting melody, calling to him.

            Luckily, a distraction named Sam Winchester walked in. His heavy gait announced his arrival far before he turned the corner. When he did, Dean was already grinning his way. “Look who decided to wake up?”

            Sam yawned. “What’re you making?”

            “Meatball subs,” Dean told him. Sam shuffled by, humming thoughtfully. “Don’t worry though,” he continued, “I also have a salad chilling in the fridge for you. Consider it a thank you for ganking the vamp that almost got my flank.”

            He snorted. “You can thank me by helping yourself to some of it.”

            “…I’m not filled with _that_ much gratitude, Sammy.”

            “Hey Dean? Did you do this?”

            Dean glanced backwards, immediately regretting it as he zeroed in on where Sam pointed. His finger poked at the dead center of the circles, eyebrow raised and ready to mock.

            He flushed, returning to his cooking. “Thought you did it.”

            “You’re the one who cares about this day more than I do,” Sam said, “Although where’d you get the red marker –“

            “I said I didn’t do it!” He slapped the wooden spoon into the pan, sauce spraying everywhere. Cursing under breath, Dean grabbed for a nearby towel, dabbing at his already ruined shirt before cleaning up the rest of his mess. He knew Sam watched him work, questions hanging overhead buzzing loudly like the fluorescents in their kitchen. Dean wished Sam would think nothing of his small outburst. But there weren’t any pearls to save him.

            Sam struck when he plated the meatballs. “So,” he started, “that was… _something_.”

            Dean sighed, resigning himself to the conversation. “Before you start your interrogation can you let me finish dinner at least?”

            “Sure, but if it looks like you’re stalling I’m asking my first question.”

            He huffed, annoyed with how well his brother knew him. Dean sped his actions up back to normal speed. Taking the garlic-and-butter painted baguette halves, he set to assembling the subs. He made two foot-long subs for the both of them, wrapping up the leftover meatballs to store for later. Replacing it with the bowl for the salad, Dean brought it to the table, shoving it at Sam. “Graze,” he muttered. After bringing over the sandwiches, Dean grabbed two bottles of El Sol before finally taking his seat across from Sam. He dug into his first sandwich; disregarding any eye contact Sam threw his way. “I didn’t do it, _honest_.”

            “But you –“

            “I _didn’t_.”

            Sam smacked his lips, a sharp puff of air shooting through his nose. “Fine,” he said, “so you didn’t do it, who cares at this point? I want to know why you freaked out like that.”

            “I didn’t _freak out_ –“

            “Dean, it was like watching Mom discover your _magazines_ all over again.”

            He winced, remembering how Mary cornered him in the library with a copy of Busty Asian Beauties in her hands and a disappointed look stretched across her face. What made it worse was how public his shaming was, with Sam and Jack having front row seats.

            Sam powered on. “If this is about how you celebrate it, I’ve _long_ accepted that’s how the day’s gonna go for you. Even if you are _forty_ and should be doing better things, I’m not going to crack jokes about it anymore.”

            Dean paused, unsure of what to do next. Sam, in his ramblings, provided him a perfect out. A path he could follow that would involve some awkward laughing, light ribbing, and only marginal choking as Dean stuffed his face fast enough to escape. Except, with one foot out and ready to go down, Dean found he couldn’t do it.

            “Actually,” Dean said, voice low and stilted, “I was… I’m not doing that this year.”

            Sam blinked at him. “What?”

            “Yeah,” he confessed, “I – uh, I never really _cared_ that much about it either. The first time it happened, it wasn’t really what I was _planning_.” Dean was only twenty, having snuck into the bar alongside John after a successful hunt. A woman with dark hair, blotchy makeup, and a pronounced slur stalked her way over and heavily communicated her wants to Dean. John looked at him with pride, winking and giving them space. He had the same expression on his face when Dean met up with him later, when the bar had closed and Suzie-Sandra-Sarah-whatever was still smoking her cigarette in the bathroom.

            “Like a chip off the old block,” John clapped him on the back, “My son the lady killer.”

            It only felt natural to keep with tradition after that. So every Valentine’s Day, Dean found himself a friendly dive where he could hook up with a stranger for the night, spend the night with another broken heart, with John’s smile in the back of his mind.

            As the years went by, the specter of John’s face disappeared further and further into the ether. And now, with only a few days before Valentine’s Day, it’s completely gone. Along with any desire Dean has to sleep with another _stranger_. There’s only one person his body called for these past few years. Very recently it wouldn’t shut up with ideas revolving around the upcoming holiday. _That_ was Dean’s problem with the calendar.

            “Then you’re going to… what?” Sam asked, “Spend the day with a tub of ice cream and a queue of romantic comedies?”

            “Don’t want me to crash _your_ fun?”

            “So get this, _I_ have a _date_ this Valentine’s Day.”

            Now Dean sat stunned. “ _You_ have a date? This isn’t, like, a joke right? Where I ask with who and you say something nerdy like a book or some file you found in the archives?”

            Sam blustered, slamming his fork down. “If you _must_ know,” Sam said, red faced, “I met her a few nights ago at the grocery store. We were in the fruits and veggies section, and reached for the kale at the same time –“

            “Aww a _meat-free_ cute.”

            “Anyway, we got to chatting and she invited me to her friend’s poetry reading at this vegan café that recently set up shop here in Lebanon –“

            “Okay you officially made me disappointed in you,” Dean told him, pushing his plate away, “What’s your hippie-dippie date do for a living? Dance in a park with a tambourine?”

            Sam wouldn’t meet his eyes. “…She works at a weed dispensary.”

            “Wow.”

            “She’s nice Dean, a little spacey but _nice_ ,” Sam said, “Besides, it’s not like you’ve got any plans now. Looks like _you’ll_ be the one waiting up for _me_.”

            Dean squirmed in his seat. “I mean… I might have plans.”

            “Do you?”

            “Not yet, but…” He sighed, scrubbing at his hair. Dean tried pushing past the stone in his throat, but it tumbled backwards into his heart. He barely managed to squeeze out, “I’m working on it.”

            “Working on it? With who? Marta the mailwoman?”

            Dean scrubbed a hand down his face, grunting out a mixed garble of frustration. He wished Sam understood that, instead of staring at him like an animal in the zoo. Every time he attempted bringing up this side of him went similarly. The feelings and thoughts that were bottled up managed to uncork themselves, only to pool behind the emotional dam he built and reinforced with developmental issues.

            After all those years of healing, Dean considered the structural integrity must have weakened. John’s surprise visit was the supposed final stick of dynamite that would blow up his walls and free all that he shoved behind them. It made some heavy cracks, but didn’t demolish anything.

            Little stuff slipped through, though. He had been more forthcoming with interests long since hidden. Instead of locking his manga and anime away in the little safe he bought his closet, Dean left them lying around now. When Mary waved his Busty Asian Beauties around he was thankful she found those and not the two or three yaoi he bought in a drunken haze. And he experimented with his wardrobe. One night he slipped his washing shorts over some lacey underwear and didn’t take them off for the entire night. Granted, Dean hadn’t left his room the whole time but that was a small step. Dean also widened his pop culture portfolio. He’d be proud to tell Sam that a pop song came on the radio and Dean kept it on, even nodded along to it. What he wouldn’t _ever_ share with Sam was how he went down a musical spiral, downloading all her work and even waiting up until midnight for her latest album drop. He didn’t regret it though, thank u, next was _life changing_.

            All those were things he enjoyed that he was no longer going to apologize for, pursuing them with wild abandon even if it seemed out of character. There was an addicting rush of freedom that came from this, with each step Dean took into the light. Like two halves of his soul was reuniting, dancing in the knowledge that Dean was finally enough for the only person who mattered – _him_.

            Crushing the pearl also crushed the burden weighing on Dean’s shoulders to be the ‘perfect son’ his father always wanted. His validation, although greatly accepted, wasn’t what he needed. Hearing John say how proud he was of him, and that he loved him, didn’t fill any special hole. Because Dean had already filled it with the family he stitched together from the tattered remains of tragedy after tragedy. They helped Dean figure out happiness cannot come from meeting an imperfect person’s expectations, but by being able to look in the mirror and love who was smiling back.

            He said it out loud, the other day. The Bunker was oddly quiet, and Dean wandered past his mirror, phone in hand. Catching his reflection from the corner of his eye, he stilled, focusing on all the fine details age had added. Dean whispered it at first, a quiet “I love you” that hardly filled the space. Repeating it, his voice grew steadier and louder; by the third and final time he declared it confidently with no trace of doubt to be found.

            And now that he loved himself, Dean figured it was time to love somebody else. A _specific_ somebody. _That_ was where his trouble lied. The biggest secret he shied away from all his life could not overpower years of trained suppression. He worked for so long already and only managed to admit certain things in the safety and comfort of his dark room. “I didn’t like Gunner _just_ for his wrestling skills” “Superman is a total nerd but Henry Cavill’s biceps could totally knock Batman off his top spot” and “Am I predictable or is dark hair, blue eyes, and a cut jaw really the hottest thing ever? Probably both.”

            Dean had the bravado of a man who would shout his heart from the tallest rooftop but when the time came found himself with a dizzying fever, sore throat, and situational amnesia.

            “Dean?” Sam asked after a long stretch of silence, “You – uh… you were talking about plans?”

            He warbled out a mournful sound, twin hands of the past loosely clutching at his neck. Dean knew Sam wouldn’t judge him for his confession. His brother ran away to California, acceptance was as common as sunlight there.

            “If you don’t want to tell me, then fine just stop with all of… _that_.”

            Dean’s frustration reached a peak. Dropping his head into his hands, he huffed a harsh breath out. Eyes closed, Dean rambled out his plans in a hoarse mumble. It was the best he could do. He was resigned that all his hard work stalled, and he had no clue how to stumble over the last milestone to break through his nerves.

            But then Sam said, “Holy shit, you wanna take Cas out on a date?”

            Sam had impeccable hearing. It always made things harder, Dean having to watch his mouth around him. And John, muttering harsh criticisms under breath, could never have the last word in a fight. He should know his golden retriever of a brother would understand all that.

            A terrified gulp and minute nod were his answers.

            The mood shifted immediately. Dean imagined, in his worst nightmares, that Sam would take this as a joke. Then, as time wore on, and Dean’s expression fell even more into unwieldy terror, Sam would deny his truth and place back upon him the expectations Dean spent a lifetime shedding. The scene was, thankfully, only a nightmare. The reality was softer.

            A wide grin stretched across Sam’s face. He reached across the table to shove Dean playfully, laughing. “That sounds awesome! What were you thinking?”

            Dean was thinking many things, none of them about his plans with Castiel. He asked, “You… you’re okay with it?”

            “Okay?” Sam parroted, “Dean, I’m more than okay with this! I’m…” He trailed off, his smile dimming. “Were you… did you think I wasn’t going to… _accept_ you?” Dean shrugged, glancing down at where his fingers danced along the edge of the table. “Dean,” Sam sighed, “I… how long have you been troubling over this.”

            “All my life?” he said, offering a weak chuckle. “Telling you though, maybe a… a few years.” Sam spluttered, but before he could speak again Dean carried on. “Look, I know… _logically_ , I had nothing to worry about. But until it was out in the open _any_ possibility could happen. Even the… even the bad ones; I’m used to those being the ones that come true.”

            “Dean, that’s… I wouldn’t love you any less because of this. I’m not –“ He stalled, unable to finish.

            He helped him along. “Not like Dad?”

            Sam cursed under breath. “He didn’t… you never came out to Dad right?”

            “After that one case in Provincetown? I knew better than that, even with him flashing forward to present day,” Dean told him, “Dad went down thinking my future was set on a loving wife, some kids, and a mangy mutt. Didn’t even consider that maybe I’d want a… _husband_.” The longer he talked about it, the easier it got. Dean sucked down a lungful of air, greedily keeping it in until forced to expel it.

            “So you’re –“

            “Bisexual,” Dean said, “I used to think it was just situational gayness. Although maybe queer would be easier – because really what _is_ Cas? He’s got a dick, but I don’t think he considers himself a man like you and I –“

            “Are you serious about Cas?”

            He paused, eyes flitting up to meet his brother’s. Sam had a shadowed suspicion reflected in his gaze, but made no move to voice it. Dean would. “I… I am, Sam. He’s it for me. I didn’t know it at first… then I didn’t want to believe it. After all we’ve been through though, there’s no one who could make me as happy as he does. No one I’d _want_ to. Cas is… _irreplaceable_.”

            Sam sighed. “I’m… thank you, for telling me this. Really.” He frowned, then. “So then your outburst was because…?”

            “Because I can’t say _any_ of this to Cas,” Dean whined, “Whenever I see him I have all these _feelings_ and they just bottleneck inside and I can’t get more than three words out.”

            “For real?”

            “Yeah, it’s all just been building up. I used to handle it all fine, but now I don’t _want_ to keep it to myself except my body hasn’t gotten the memo yet.”

            Sam hummed, leaning back. “Well, Valentine’s Day _is_ almost here… if you’re going to do something better do it now.”

            “Yeah, I think that’s obvious.”

            “Cas isn’t going to say no.”

            “And you know that?”

            “Yes, I know it… and I’m sure _you_ know it, too. Right?”

            Groaning, Dean hid his face behind the cage-like bars of his fingers. “So I’m not seeing things, then.”

            “Seeing things?”

            “I don’t know… I’m pretty sure he feels the same way but then I start doubting it. Cas is a pretty intense guy, right? Isn’t he like that with you?”

            He scoffed. “Dean, Cas is intense around _you_. I could list all the things he does with you and _not_ me but by then we’d be hedging on Saint Patrick’s Day.” Standing, Sam walked over to Dean and laid a hand on his shoulder. “Listen, you ask Cas or you don’t ask Cas – that’s your call. But what you did now I… I’m still happy. I couldn’t _imagine_ the you who showed up on my doorstep four years after I ran away saying stuff like this and us being _serious_ about it. We’ve… we’ve grown a lot.”

            Dean clapped his own hand on top, squeezing Sam’s. “Yeah, well there’s only so much alcohol can do before you have to take a cold, harsh splash of reality.”

            “But it’s better than booze, right?”

            “I mean I don’t get hangovers from it but… yeah.”

            Sam dropped down to hold Dean in a tight hug, which he returned. Pulling away, Sam cleared his throat. “Have you told anyone else or –“

            “Not yet,” he said, “And I’m not sure if I want to just yet. I’m…”

            “Working things out on your own time?”

            “Yeah.”

            “All right,” Sam walked away, “Thanks for dinner, it was great. I’m gonna be in the library if you need me.” He was at the door before Dean called for him. “What?”

            Dean shot him a tight-lipped smile. “…Thanks.”

            “…No problem, Dean. Literally.”

            He tried leaving again, only for Dean to stop him with one last thing. “ _What_?”

            “I wanted to offer you some brotherly advice, y’know… since you gave me some.” He coughed out a chuckle. “When you go on your date, y’might want to bring protection?”

            “I think I’m old enough to know how condoms work, Dean.”

            “I was thinking more like a knife or a gun,” he continued, “Knowing how your hookups tend to go, either you might need it or she will.”

            Dean was red-faced from holding back his laughter, only for it to all tumble out of him at Sam’s deadpan expression. “And you killed it, Dean,” he said, “You ruined our perfectly good bonding moment.”

            “Sorry, but I had to!”

            Sam flipped him off, “I hope Cas appreciates your humor.”

            “You know he does!” Dean yelled at his retreating figure. Alone once more, Dean stared at his second sandwich long since gone cold. He repeated the scene that unfolded, wiggling in delight at how everything went. Uncaring to its temperature, Dean dug into his dinner. His mind was focused on other things. With renewed vigor, Dean vowed that he would figure out a way to ask Cas on a date. He had to.

**Notes for the Chapter:**

> So if anyone can guess who I based Sam's 'date' off of (an actual real life person) they can get some *imaginary* celery and rose... *hint hint wink wink*


	2. Mary

            Sleep, in theory, would have done wonders for Dean. Unfortunately, he couldn’t find any. After his conversation with Sam the other night, he committed to thinking up a date that would be perfect for him and Cas. Alongside that, Dean practiced _how_ to ask him. An hour before his head hit the pillow, he pretended his reflection was Cas and flubbed through countless attempts until tiredness caught up to him. But once he started, he couldn’t stop. He tossed and turned, mind on a runaway track that reset every time it went off the rails. Dean managed to put two hours under his belt before his alarm blasted to life.

            Unable to get back to sleep after that, Dean decided coffee was the best, most appropriate step to next take. He shuffled down the hall, tying a loose knot over his robe. Nearing the kitchen, the bitter aroma of coffee drifted downwind. Dean hurried his pace, the scent already kicking him into gear. Rounding the corner, he found Mary pouring her own mug.

            She looked up, smiling. “Want me to pour you one?”

            He nodded. “Please.”

            “Get the cream and sugar.” Dean collected them while Mary pulled another mug out. Placing the items down, he waited for her to carry both mugs and join him at the table. He let her doctor her coffee first, one spoonful of sugar and a splash of the cream. Dean went overboard, tossing in three heavy loads and a downpour compared to his mom’s light sprinkle. Mary raised a brow as he stirred them all together, his drink now considerably lighter than hers.

            “What?” he asked.

            She smirked. “No straight black?”

            Dean rolled his eyes. “Not if I have the choice.” After a few healthy sips, he cleared his throat. “So, what’s on the agenda today?”

            “Well,” Mary started, “I was going to scan the web for any strange sightings, pass it along the chain for any hungry hunters out there.”

            “Not going on one yourself?”

            She shook her head. “Bobby wrapped up a rugaru hunt last night, should be back here in time for lunch. He – uh… said that it might be fun if we do something together, later on in the week. So I don’t want to start a hunt that might run longer than we’d want.” She glanced at the calendar, eyeing the glaringly red circled.

            Dean tracked her gaze, smiling. “Really? I figured a case would be the perfect date for the two of you.” She blushed heavily at the accusation, taking more interest in her coffee than him.

            He didn’t mind, though. As mentioning the very word spiraled Dean back into his own stormy thoughts. The clouds in his head darkened with new knowledge that even Bobby managed to make plans for Mary on Valentine’s Day. Dean, so lost in his own thinking, couldn’t hear Mary’s coughing. But he felt her kick under the table

            “Ow! What was that for?”

            “You weren’t paying attention.”

            “And there was no other way?”

            Mary sighed, “Could you focus, please? I have something I want to ask you.”

            Her tone sucked all the levity out of the room. Dean straightened in his seat, frowning. “What’s the matter?”

            “Well,” she said, “I wanted to ask your opinion about Bobby –“

            “Ma, like I said before, if you and him wanna explore something I’m more than fine –“

            “No, no,” she stopped him, “I – uh… I was going to ask how I should approach telling him about – about _John_.”

            His eyes widened. “You haven’t told him about Dad yet?”

            She drew into herself, finger sliding back and forth on the rim of her mug. “I’ve been meaning to,” Mary confessed, “I felt like it should be an in-person discussion. But when he came back to the Bunker he was exhausted, and I figured I’d leave it for the morning. Except when I woke up he was gone! He was making us breakfast and, well, it looked nice and the story would only ruin it, and I could wait until after. Only…”

            “After never comes,” Dean finished for her, "I’ve been there… you’ve come to the right place.”

            “So? Should I tell him when he gets back or put it off at least until Valentine’s Day is over. I know it’s important but I don’t want to make things awkward between us.”

            “That’s going to be pretty hard when the topic of your conversation is about your dead husband who came back and would have stayed if the timeline wouldn’t have been messed up.”

            She sighed, leaning heavily against the table. “Better to rip the Band-Aid off quick, then?”

            He nodded. “It’s the only way, especially with stuff like this.” At his mom’s downtrodden expression, Dean continued. “I don’t think it’d be that bad, though. This Bobby had a dead wife, too, right? In our world, our Bobby did. And one day his wife came back to life – she was a great baker, reminded me of you when I believed you could cook.”

            “What happened to her?”

            “She – ah… she got put back in the ground,” he said, “Karen and all the others in Sioux Falls were zombie-ish. Their resurrection was another sign of the Apocalypse. Bobby… he didn’t want to send her away, but Karen knew she had to go. It’s normal to want second chances with people they love, to say and do what you couldn’t the first time around…” He had shown too much of his hand. Dean’s voice wavered and his hands shook. Setting the mug down, Dean pulled himself out of the dark hole he dug himself. “Bobby’ll totally understand where you’re coming from. What you’ll really need to apologize for is waiting so long to tell him.”

            Mary watched him, features shifting between concerned mother and curious hunter. Deciding on one, Dean was thankful she landed on the former. _As_ thankful as someone can be, when really either option was a nightmare waiting to happen. She reached across the table for his hand, slipping it into hers easily.

            “Have you got something to get off your chest, too?”

            Dean hummed. “What makes you say that?”

            “Call it a hunch. Or mother’s intuition.”

            He squeezed her hand, staring at it instead of her face. “I – uh… Since we’re talking about relationships and all…” Wetting his lips, he rushed out a breath. “I’ve been thinking about taking the next step with – with _Cas_.”

            Mary cooed, “Oh honey.” Bringing her other hand forward, she trapped Dean’s hand in her grasp before drawing it closer to her. “You and Cas?”

            Nodding once more, he offered her a shaky smile. “Yeah, I… I want us to be more than friends. Because I – um… I-I’m _bisexual_. I like girls and I like guys. But I especially like Cas.”

            “A lot?”

            “A lot a lot.”

            Mary giggled, tapping a finger against his skin. “You’re sounding like a kid.”

            He blushed at her observation, giggling as well. He reveled in the wondrous feeling, a radical change from how it went with Sam. Especially since it was his second time coming out, and they took place less than twenty-four hours apart. It wasn’t what he expected to do, when waking up. But he’ll take the win. “I guess that’s how I’m feelin’. I mean, most of my life I wasn’t able to be a kid – I think I deserve a few days here and there.”

            Her smile dropped like a switch was flicked. Her posture went rigid, and her grip around his hand tightened.

            “Hey?” he asked, “You okay?”

            She shook her head. “You know… sometimes I forget how you and Sam were raised –“

            “Ma…”

            “And I can’t say sorry enough,” she carried on, “Seeing John again, how he was acting with you boys… now that _I_ was here. It really drove home for me how much my death changed him. He was exactly like I remembered… which only made it worse. Because after he left, all the times you and Sam told me about your past came back to me and – and I would recall reading something in the journal… I can’t help but feel at _fault_ for all of this. That the reason we’re apart is all because of me. And that you and Sam had to grow up like you did…”

            Sighing, Dean freed his hand to pick his mug up again. “You can’t blame yourself for that –“

            “But I deserve it – _you_ deserve to blame me for – for –“

            “I have.”

            She paused. “You have?”

            “I have,” he repeated. “But you know what I did? I took the blame I placed on you – on _Dad_ – and I chucked it off the nearest canyon so it could go fuck itself.”

            “…Why?”

            “Because it’s heavy,” Dean said, “Heavy and pointless. All it’s been doing was dragging me down; keeping me in this same, dark place that was just _suffocating_ me. But now I can fucking breathe. I’m moving on from all of that, focusing on what’s happening now and who’s around me. Because _that_ deserves my attention.”

            Mary smiled at him, water collecting around the edges of her eyes like a leaky faucet.

            Dean drank the last of his now cool coffee, reflecting on what he said. It was true when he and Sam whispered to each other, near moments before John disappeared back to 2003, and it’s the same now. In this stage of the game, for Dean blame was a distraction. He could not let it hold him back from fully embracing all that life offered, both the good and the bad. If he did, it would count as a win for all the dark voices that echoed throughout the past four decades. Dean held his middle finger up at them for the four-year old whose house burned down, that had responsibility thrust upon him at too young an age. For the ten-year old who learned that being an expendable little soldier was more important than being a son. For the fifteen-year old who experienced as much of a ‘normal’ life as he could before signing back into service. The best revenge against his childhood traumas was the comfort he felt in his own skin.

            Mary broke their shared silence. “You’re very wise for someone who’s supposed to be the _child_ in this relationship.”

            Dean shrugged. “Better wise than a wise ass… been called _that_ too many times, it gets old.”

            She snorted into her drink. “Well wise one, do you have any suggestion on how to resurrect the mood after we killed it?”

            He rolled his eyes. “Well, we could talk about _our_ Valentine’s Day plans? Do you know what Bobby wants to do?”

            “No,” Mary said, “But knowing him he might want to spend it outdoors… we did that a lot back at Donna’s cabin. Some days we’d get out as the sun rose above the trees and wouldn’t come back until hours after it had already set. I think he’s more comfortable when there are no walls, because then there’re no surprises.”

            “He’ll get used to our world one day,” Dean told her, “I’m sure of it.”

            “Anyway, it’s time to turn the tables.”

            “Oh no…”

            “What do _you_ have planned for Cas?”

            Dean groaned, hiding behind his hands. “I had hoped you wouldn’t ask me that.”

            “Angel got your tongue?”

            He peeked out from behind a few fingers, glaring at her with no heat behind the eyes. “You know, you’re taking this very well for someone who was born in a different time.”

            Mary shrugged. “I’ve _always_ been fine with it. When you grow up knowing that monsters exist, things like religion, politics, and sexual orientation really don’t end up mattering a whole lot. What does is how we treat each other; make the most of our time here. And I’d rather dedicate my energy and my anger towards the things that _deserve_ it.”

            “I wished more hunters were like you,” Dean told her, “You wouldn’t believe the men and women who I’d run into, who’d pass over a case just because victims were different than what they’d consider ‘ _normal_ ’. When I got old enough, I did my best to take those cases on but… there was never enough time. Never enough help.”

            “Are you talking about –“

            “He… I don’t think Dad would have liked me, had I come out to him,” Dean said, “Said a bunch of stuff about… about people like me. That’s some of the stuff I’ve been letting go of.”

            “Dean,” Mary sighed, reaching for him once more, “Maybe if I were still alive –“

            “We’d have still lived in Kansas, Ma,” Dean joked, “I probably wouldn’t have said anything ‘till I was this old anyway, either. At least now I feel like if I hold Cas’s hand I won’t be public enemy number one on the spot.”

            “…He would have come around eventually.”

            “Do you mean it or do you hope so?”

            Her answer was the tight line her mouth formed as she huffed a breath through her nose.

            “It’s okay,” he said, “it’s not like he can do anything about it now.”

            “I know… still, it’s stuff like that which makes me wish John could have stuck around a bit longer… all we talked about were the good old days we – we never really addressed all that happened _after_ my death. There’s a lot I need to say I didn’t get the chance to.”

            “A few years ago, we were on a hunt that involved a therapist. She was a shifter, and could take on anyone’s appearance… I’m sure if you pay her you could get everything off your chest.” He smirked, “Or, y’know… write it in a _journal_?”

            “Very funny,” she said, “Is that what cream and sugar does to you? Turns you into this sarcastic, emotionally insightful man?”

            “That’s giving too much credit to the coffee.”

            Mary stroked her thumb across his hand, smile dim under the high-powered kitchen lights. “Crazy,” she whispered, “How I can love the man and hate him in the same breath.”

            “You wouldn’t hate who he became if you never loved who he was. Dad was a shitty guy who did shitty things, and even _I_ still love him. If I didn’t… if I had dropped him the second I could, I wouldn’t be here with you. I wouldn’t have gotten this chance to get over all the stuff he dumped on me. I’d never have met the man I want to spend the rest of my life with.”

            “The rest of your life with?” she asked, “ _That’s_ the next step?”

            “Well when you know, you know.”

            “That’s true…”

            Dean gnawed at his lip. He wanted to share with her something about John as well, and was motivated by her own confession. “I also kinda wished we got more time with Dad.”

            “You do?”

            “Yeah,” he said, “I didn’t want to rock the boat then, but if I knew he was back in a way that _didn’t_ mess with time… maybe I’d say all I couldn’t. Introduce him to Cas – the better Cas, the one who knew me…”

            “I think your father would have liked him.”

            “Really?” he chuckled, “I mean, I was shocked he didn’t berate us for trusting people who _weren’t_ human.”

            “Your father and Castiel wouldn’t have clicked right away,” Mary said, smiling, “John was stubborn… I think he would have seen him as a threat and tried to prove he was the bigger man. Prove that, if it came down to it, he'd be able to protect you boys. But one way or another they’d find mutual respect.”

            “Until I told him that I was in love with Cas…”

            “You haven’t even told _Cas_ you’re in love with Cas.”

            “…I’m working on it.”

            Mary leaned her chin against her fist, grinning lazily at him. “I’m glad you’ve found someone like Castiel,” she told him, “I’ll admit, when I first met him and saw how you two danced around each other, there was… I had suspicions. I figured if there was anything there, you’d have told me. And as I got to know him better, the more I realized how perfect he was for you. He’d go to Hell and back for you –“

            “He already has.”

            “And he’d do it again,” she sighed, “There’s no two people who deserve happiness than my boys. And for you, part of that happiness involves Cas.”

            Dean matched her smile with his own. “It sure does.”

            “So,” she slammed her fists onto the table, “as part of my motherly duties, why don’t I help you figure out your Valentine’s Day plans!”

            He blanched, backing away. “I’m sure you have better things to do with your day –“

            “Nonsense. I’ve got a ton of time to kill before Bobby gets back. And at least it’ll give us the chance to do something we never got to do.”

            He should be embarrassed. When Mary walked across the table to slide in next to him, bursting his personal bubble so they could discuss different ways Dean could tell Cas or ideas on where to take him on a date, it should have been mortifying. Except Dean felt none of that. Complimenting her enthusiasm, Dean responded lightning quick to her suggestions. Like before, he felt years younger because of this. He knew that this was exactly what he meant by leaving the past where he is. Instead of mourning the youth he lost, Dean made up for it by living it now.

            And when he and Cas shared their first date, he could only imagine how young he’d feel.

**Notes for the Chapter:**

> *This was the most difficult chapter for me to write*


	3. Jack

            Dean had less than a day before Valentine’s Day was upon him. And he _still_ had no clue on how to approach Cas. Even with help from Sam and Mary, Dean couldn’t find the paddle to guide him down the rapids. The Internet – in all its power – offered no solution for him either. He blindly searched down its many holes, wasting time with each wrong turn. At least his frustrations could be drowned with food or drink, the best reason for setting up in the kitchen.

            What wasn’t working for him was how easily he was interrupted. Which was the case as Jack entered in his own funk.

            Knowing he wouldn’t be able to focus with how low Jack’s shoulders had sunk and the terrible pout affixed on his face, Dean pushed his laptop away and swung around to face him. “Something the matter Jack?”

            As if recognizing he wasn’t alone, Jack spun around, facing Dean with a blank expression. “What gives you that idea?”

            “A lot of things,” Dean said, “Now, you wanna share with the class or are we going to do the little song and dance where you lie and I ‘believe’ you and then you go and sulk until I barge in?”

            Jack sighed, slumping against the fridge. “I’ll talk.”

            “Atta boy. Grab us some sodas and take a seat.”

            He did as told, sliding a can over to Dean before setting down across from him. Jack eyed his open laptop. “Are you sure you want to talk now?” he asked, “If you’re busy…”

            Dean sighed, shutting it closed. “I’ve been staring at this since I woke up. I need a break before I drive myself insane.”

            “What are you doing?”

            “None of your business that’s what I’m doing,” he told Jack, “Now, are you gonna keep stalling or are you going to explain why you’re acting like someone knocked all the air out of your balloons.”

            “I can assure you it wasn’t that.”

            “No, what I meant was…” he huffed a laugh, rolling his eyes. “Never mind, tell your story.”

            Jack does. His explanation took them back to a few days ago, when Sam asked him to run an errand into town. “It was strange, but Sam said I’d have better luck with the lady at the mail desk than he would.” He also tossed Jack extra money for lunch. So after retrieving the package, he swung by the nearby pizzeria.

            There weren’t many people inside, but nearly all of the customers were teens. Jack felt most of their eyes on him, as was the case. “When I still had my powers, I could sense their curiosity. Who I could be since I didn’t go to school and hung around with you, Sam, and Cas; they had lots of theories about us.”

            “Yeah, I know.”

            “Anyway, so I was waiting for my pizza…”

            There was a tap on his shoulder. He spun around, coming face to face with a boy around his age only taller by him by a few inches. A colorful hat that had a little poof at the end obscured half his face, and his tan jacket ended halfway above his knees. He introduced himself as Eliot, leading with how he knew Sam and Dean.

            “Eliot? Were there also two girls there? A platinum blonde and a tan girl with a ponytail?”

            “Yeah, but they watched from afar. I think they were too busy holding hands to join our conversation.”

            As Jack continued, he reached the crux of his problem. “After a lot of awkward silences, he wanted to see if I’d like to come to this party these kids were throwing. Said it might be nice to meet new people, since it must be lonely being the only teen that hung around adult men. I explained that I knew of kids my age who did what I did, and he seemed both intrigued and disappointed. I didn’t want to hurt his feelings, so I told him I’d go. He looked very happy –“

            “Jack, if you don’t want to go no one’s forcing you.”

            “It’s not that,” he rushed to say, “I am curious how other teens – teens that _don’t_ hunt – spend their time. Except as I was about to leave he said he couldn’t wait for our _date_.”

            Dean blinked. “Oh.” He leaned forward, brows drawn forward, “So do you feel… _weird_ to be going on a date with a boy?”

            “Kind of,” Jack confessed. Dean’s chest constricted, heart beating wildly out of control in his chest. However, it was all an overreaction. “I start getting dizzy, and keep thinking about all these things that could happen. Like what if he wants to kiss – or, or have sex? What if he wants to drag me to his undead boyfriend and feed me to him –“

            “Jack that was _one_ time.”

            “But isn’t it Winchester luck for stuff like that to happen?”

            “Only if your first name is Sam,” Dean joked, “Jack, it’s not _weird_ to be nervous with these kinds of things.”

            “That’s exactly it,” Jack said, “ _Nervous_. I… I’ve never gone on a date before. At least, one that _wasn’t_ for a case. It’s thrilling and… _thrilling_. Since then I’ve been doing research – watching movies, reading books, looking through blog posts. And just so I wouldn’t forget, I even left a small reminder for myself.” Jack glanced at the calendar, at the harsh red circles around Valentine’s Day.

            Dean shot him a mock glare. “So that was _you_.”

            “Should I… _not_ have done that?”

            He waved him off. “Public space. Doesn’t matter.” Leaning forward, Dean folded his hands across the table, “What _does_ matter is that you have a date with a boy – a boy it sounds like you _like_.”

            “I… think so,” Jack told him, “He looked… _cute_. And when he told me what he first thought of me, something about _Bambi_ and _doe eyes_ … my face felt very hot. I figured it was embarrassment, I’m very used to that feeling.”

            Dean shrugged. “I know what you mean, if I had a nickel for every awkward moment between me and a guy I found hot…” He chuckled, shaking with mirth. Jack’s story reminded him of different points of his life. Being sixteen and fighting down a boner before facing off against his teammate with dimples that could kill. Twenty-three, on a solo hunt, and nearly giving himself away because the shifter wore Val Kilmer’s face from ‘Tombstone’. Countless of deputies and sheriffs, Aaron, and especially a hilarious montage of the adventures he shared with Cas flashed to mind. Not all of those memories were shiny jewels, in fact most were colored with fear, confusion, and shame the first time around. Now, though, he thought back on them all with a profound fondness.

            When the highlight reel went blank, Dean came back to the present finding Jack with a curious gleam in his eye. “What?”

            “You’ve found guys hot?”

            He snorted. “Tons.” Once more, Dean found himself coming out in the kitchen. “Especially around your age. It was like they were everywhere I looked. Probably because we traveled a lot…”

            “Did it get easier?” Jack asked, “I mean… over time, talking to them?”

            Dean paused at that. He pouted, drawing into himself. “Well,” he started, “Actually…” He reached one hand behind him to scratch at his neck. “It’s – uh… I’m still pretty bad at it.”

            “Really?”

            “Never had the opportunity to _practice_ ,” Dean continued, “Didn’t really _want_ to feel this way… back then, especially where my Dad used to take us. The places I lived weren’t kind for folks like us. Was easier to stick to girls. And even when I had some freedom I just… never acted on it. Always felt like _someone_ was watching… that it might get back to… certain people.” Things would definitely have been different if John found out about Dean’s interests.

            Which made him really proud that he had this moment here with Jack. Because now _he_ was the father figure, and he could be there for Jack in a way he wished John were for him. If there’s one thing he was thankful about John was showing him all the ways he _shouldn’t_ treat a kid. “And you,” he looked back up at Jack, “You’re really lucky. Things have changed, and it’s easier to be yourself – at least with _us_. You have people who’ll understand and love you no matter what you’re going through. We wouldn’t toss you aside over something like liking a boy.”

            Jack’s face softened. He smiled, cheeks rosy. “…Thank you, Dean.”

            “So?” he asked, “How are your nerves now?”

            “They’re much better,” Jack said, “But I still have no idea what I’ll be doing.”

            “No one knows what they’re doing, especially teenagers. All you need to know is no means no and you don’t owe anyone _anything_.”

            “I’ll keep that in mind.”

            Dean cracked open the can of soda, taking a sip of it. Jack mirrored him, with both dropping their drinks at the same time. He rolled his eyes, stifling a snort. From the beginning, Dean noticed how much Jack tried to be like him. And over time, he enjoyed being able to teach Jack all sorts of things. From driving to which shows he should watch, girl talk and now boy talk; they were things he never imagined he’d get to have. When he was with Lisa, he let himself believe that one day he’d do the same with Ben. But as it turned out, it wasn’t the right time for him to be a parent.

            “Hey Dean?”

            “Yeah, Jack?”

            “Can you tell me what you were doing on your laptop now?”

            An immediate shut down was hanging off the tip of his tongue, but faster than he could speak Jack fired off a powerful set of puppy dog eyes that were made to break through Dean’s defenses. “Damn Sam,” he groaned, “Should never have let him teach you that…”

            “Please?”

            He crumbled, slumping in his seat. Dragging his hand up his face, fingers then raking through his hair, Dean told Jack what was going on. “I’m… tryna come up with the perfect date to take Cas on for Valentine’s Day.”

            Jack straightened immediately. “ _Oh_.”

            “You’re not,” Dean stuttered over his words, face flushing as each second passed, “You don’t find it… _weird_ , right?”

            “What’s there to find weird?”

            “Me asking your dad on a date?”

            “Dean, you’re also my dad. There’s nothing weird about it.” Jack said it so simply he thought he had misheard. But his words sunk in, and a grin crept its way onto Dean’s face.

            “You… you really think so?”

            Jack nodded. “You, Cas – and Sam – I consider you all wonderful father figures.” He frowned then. “Of course, if you were to ask Sam on a date, then I would find it weird –“

            Dean choked on his soda, some of it spraying out his nose. “No!” he coughed, “Nope, that is – that will _not_ be happening.” He eyed Jack strangely. “You haven’t been on weird parts of the Internet that talk about us have you?”

            “The Internet talks about us?”

            “Never mind.”

            “You know Valentine’s Day is tomorrow, Dean,” Jack said, “I’m pretty sure most people have already made their plans and reservations.”

            “You think I don’t know that?” Dean sighed, “I’m driving myself up a wall trying to find something that Cas’ll like. But every time I think I’ve settled on an idea, I keep thinking of all the ways it could go wrong and end up back at square one. I just…” His voice grew smaller, and he tapped at his half-filled can. “I want to give Cas the date he _deserves_. He’s a special guy, and I want to make him feel special ‘cause whenever I’m with him and he – he stares at me like he does, that’s how I feel.”

            Jack smiled at him. “That’s… really sweet. Are you sure you haven’t gone on dates with guys before?”

            “Believe me, I wish…” Dean turned his head, looking out into the empty kitchen. “It’d be easier, I think then. Coming up with a date. Instead of stressing over how _perfect_ it’s all gotta be. Because this wouldn’t just be our first date, it’d also be _my_ first date with a guy and… hell, forty years in the making I want it to go over well.”

            Jack called his attention back to him. “I think you should take your own advice.”

            “What do you mean?”

            “Well, to me it seems like you’re _also_ letting your nerves get the better of you. And you’re making things more complicated then they need to be.”

            “Really?”

            “Of course,” Jack said, “This is my first date with a guy… and it’ll be surrounded by a bunch of kids who – from what I’ve seen on TV – will most likely be drinking, dancing, doing drugs and ultimately have the cops called on us.”

            “…You’re really making me have second thoughts on letting you go.”

            “But none of that matters,” he carried on, “because I’ll be with him and… as long as he focuses on me and makes me feel special, then the atmosphere won’t really matter, will it?”

            Dean blinked, drawing out a long beat before chuckling. “You’re making a lot of sense there, kid.”

            “I had to at some point,” Jack shrugged, standing. “I think Cas will like wherever you take him because he always looks happier whenever he spends time with you.”

            “He does?”

            “It’s in the eyes,” Jack told him, expression deadly serious, “Everything is about the eyes. When they focus on the male lead’s face in the movies I’ve watched, they become glossier and glow. It always struck me that I’ve seen that happen before, but I couldn’t place it until now. You both do it to each other.”

            He scratched at his wrist. “Glad to know I’m subtle…”

            “Subtlety’s overrated,” Jack said, “In my experience being direct is much easier.”

            “And here _I_ thought I was doling out the life advice.”

            “It’s good you find my words helpful… I was feeling bad, you giving me all that wisdom and I had nothing to repay you with.”

            Dean blustered, frowning. “Jack, I’m your _dad_. You don’t _owe_ me anything. It’s part of my job to help you when you need it. You don’t gotta ‘repay’ me… you just gotta pay it forward when you have a kid of your own.” Thoughts racing, he jabs a finger at him. “Which isn’t anytime soon because condoms are your best friend, capisce?”

            “Understood.” Then, Jack leapt forward and wrapped his arms around Dean’s shoulders. Dean froze, but slowly returned the hug. “You’re a good dad, Dean,” Jack whispered, “I wish you could’ve had someone like _you_ when growing up.”

            Dean smiled, a wistful crack across his face. He willed the tears back, sniffling. “I used to wish for that, too. But if that were the case, then so much would be different. Sometimes we’re dealt a hand we gotta play, and we make the best out of it. And from what I can tell, I’ve got the best in my life right now.”

            Jack pulled away, then. “Thank you, Dean.”

            “No problem, kid. And… thanks to you, too. I – uh… I’m here if you need me.”

            He nodded, moving towards the exit. “I’ll remember that. Although now, I think I’m going to pick out an outfit for tomorrow.”

            “Plaid is always a safe choice!” he called to Jack’s retreating figure. Shaking his head, Dean drummed his fingers on the table. His spirit was lifted after his talk with Jack, reminding him even more of what he got to keep by crushing the pearl. It wasn’t just his and Sam’s close relationship, or a second chance with his mother, or even a best friend he loved with all his heart, but a _kid_.

            From what he learned growing up, Dean thought being a father was impossible while also being a hunter. And to put a child through what he had to face… it was one of Dean’s nightmares. Sam was the closest he had to a kid and he made peace with that, more so after his failed attempt at normalcy with Lisa and Ben.

            Jack was his chance to be the dad he always wanted to be. To have moments that weren’t few and far between like his and John’s fishing trips. He represented the normalcy that could be found in a hunter’s life. Inspiring Dean to complete their little family by better affirming Cas’s place in it.

            Just then, an idea came to mind. Dean’s face lit up like a switch was struck. “Wow… I can’t believe I didn’t think of it before…”

**Notes for the Chapter:**

> *This was really fun for me to write - I love Jack and Dean's dynamic*


	4. Cas

            Dean figured he made the right choice. Granted, Cas didn’t eat. But that hadn’t stopped his angel from saying yes. When Dean asked earlier in the day, Cas seemed excited to come with him to the B&E Pizzeria. There was slight hesitation, in which Dean’s heart ceased to beat. But then Cas skewed his head, smiled, and agreed to go. Before he ruined it by jumping from glee, Dean fled the scene. They only reunited minutes before leaving the Bunker.

            There was a slight hiccup, however. When they arrived, the place was crowded. He recognized Max’s mom, Caitlin, working as host in the front. Dean moseyed over with Cas in tow, expression friendly, asking if there was a seat for them.

            “I’m sorry,” she said, “But we’ve got a ton of reservations, wait would be over an hour.”

            Crestfallen, Dean backed away and into Cas.

            Cas squinted at him, frowning. “Is everything all right?”

            “No… apparently today _every_ place runs on reservations, even pizza joints.”

            “That’s okay – we can go somewhere else.”

            Plans thrown from their tracks, Dean’s face sunk further into depressive features. Logically, they _could_ go somewhere else. But he planned on this specific place, and with the slight deviation his nerves were already strangling him. Cas noticed this however, and smiled softly.

            “…Give me a moment.”

            Cas walked over to Caitlin, speaking to her in hushed tones. Dean watched them, gaping when she grabbed two menus and started guiding them to a table. He looked back to Dean and nodded for him to follow. Unable to speak, Dean waited until they were fully seated before leaning close and whispering. “What happened?”

            “You said this place had reservations,” Cas said, “Well… she _happened_ to find our names there.” He smirked, eyes twinkling with stars of mischief.

            Dean huffed a breathless laugh behind his menu. “You pulled a Jedi Mind Trick on her?”

            Raising his hand, Cas pitched his voice a couple octaves higher. “These are not the droids you’re looking for,” he said, “And we do have a reservation, under Winchester, you should check again.” Dean dissolved into full-blown snickering, Cas blowing a puff of good-humored air out from his nose.

            After that, with Dean satisfied and nerves calmed, they had a wonderful dinner. Conversation jumped back and forth through a grocery list of topics. At first they discussed the restaurant, all the people there and the general atmosphere. “It’s all very… pink,” Castiel observed after Dean gave his order, eyeing the paper-maché heart dangling at the center of the room.

            Dean flushed, chomping down on some of the complimentary bread. “It’s all kinds of corny,” he said, “But it can be sweet.”

            There was a question on the tip of Cas’s tongue, Dean could tell, but with a shake of his head he decided against it. And then, before his curiosity went ahead of himself, Cas glanced behind Dean and frowned. “We’re being watched.”

            Eyes wide, he craned his neck as far back as he could. “It’s good,” he sighed, smiling, “Just Max.” She waved at him, and he saluted back. Max, along with Stacy, then grabbed about ten boxes of pizzas before heading out.

            “Max?” Castiel asked, “Oh… that girl you mentioned, who stole Baby?”

            He grumbled, “Don’t remind me.”

            “That was an obscene amount of pizza though. Do you think they’ll be able to finish it all?”

            “Teenagers can eat anything,” Dean shrugged, “But I’m pretty sure they’re grabbing it for this party Jack told me about.”

            “The one he’s going to tonight?”

            They left before Jack, who sat in the library watching the clock. “I don’t want to be early,” he said, “And all my research says I need to get there ‘fashionably late’. That way I can enter in slow-motion.”

            He spoke so earnestly, that if Dean had the time he wouldn’t have been able to burst his bubble.

            With Jack as a way in they then transitioned into family and their plans. Mary, having guessed right on Bobby’s plans, wasn’t seen at all. They left early, as Dean found out, to spend the entire day on the lakeside. Around lunchtime she texted Dean pictures of a well furnished picnic by the water, and wished him well with his own date later tonight. Sam said his good lucks in person, heading out in the late afternoon. All of this held them over until their pizza arrived. Dean, too worried about their date, barely ate prior to now. So before the waiter could leave them he dug into the pizza.

            Halfway through his second slice he noticed Cas gazing at him, hands clasped under chin. Dean smiled, cheeks rosy and filled with gooey cheese. He swallowed. “I – uh… probably need to slow down.”

            “If you want,” Cas shrugged, “I’m quite _used_ to your eating habits – or rather the lack thereof.”

            “You really know how to make a guy feel all warm inside, Cas.”

            In a moment of humanity, Cas pulled back. His eyes dipped downward as his hands searched for something to do. One ran through his already wild hair while the other tugged on his tie while he huffed out near silent laughter. Dean gulped, in awe of his angel’s presence. In the corner of his eye, a memory flashed of them being in this same restaurant not too long ago. Except it wasn’t Cas there with him, it was _Castiel_.

            Castiel, the angel he used to be – Heaven’s lapdog and enforcer. Bearing down on him with all the force of a hurricane, battering Dean every which way. Who was completely immune to any pleas of mercy because he was _nothing_ to him. He never pulled Dean out of Hell, never saved the world, never fell from grace nor became his friend. The Cas he met all those years ago and the Cas in front of him now were two completely different people. And Dean would shatter thousands of pearls to keep the latter close at hand.

            His thoughts must have shown on his face, because Cas was leaning across the table, asking if he was okay.

            “Just remembering,” he said, “you know how I told you ‘bout Dad coming back? And the changes on the timeline?”

            “…I do.” It was a strange affair, after. When Dean finished telling Cas the story, his angel hadn’t said a word. He raised a hand towards Dean and healed his wounds before going off on his own. They hadn’t spoken to each other for two days before Cas came back, shoulders heavy, apologizing for what he did. He saw some of that melancholy returning now.

            “Well, when we met… for the first time – uh, it was… _here_.” His throat was scratchy, and even sipping at the water in his glass wasn’t helping.

            “When I…” Cas whipped his head around, frowning. “I don’t… why would you take me here?”

            Dean sighed, Cas’s question familiar to him. He asked himself the same thing when checking the pizzeria’s hours. His answer hadn’t wavered. “Because it reminded me how important the smallest of changes can be. Since you didn’t meet me, you weren’t… _yourself_. I had almost completely forgotten how much of a stick-in-the-ass angel you were. Made me appreciate all the more who you are now, what we went through, and the… the better people each of us brings out in the other. I mean all you were supposed to do was raise me from perdition. Yet you stayed. You fought against all you knew, your brothers and sisters, _destiny_ … for…” He wanted to say ‘ _me_ ’, but his tongue slipped out “this” instead, hand waving around for extra measure.

            With his stream of consciousness ended, Dean stuffed more of his pizza down his throat so as to stop himself from adding to his already emotionally vulnerable monologue.

            Cas, almost at a loss for words, offered a meek ‘okay’ before returning to silence. They stayed like that for some time as Dean powered through another three slices. So as to have something to do, Cas grabbed a slice as well. He only took one bite from it, but tearing at the crust was something he did with fervor.

            With a full belly, Dean pushed away the last two slices. “Y’know, there was a time I could wolf down two of these pies on my own,” he said, burping, “And now? I think I have heartburn…”

            The waiter swung by again. Dean balked at dessert, earning a sweet chuckle from Cas. “Just the check,” he said, waiting until they were alone before turning to Cas. “Hey,” he murmured, “Was this… okay?”

            “Okay?”

            “Like did you have a good time?”

            Cas smiled. “I always have a good time with you, Dean.”

            Heart fluttering, Dean answered with a grin of his own. His cheeks hurt with how wide they stretched. “Yeah – I mean… _same._ ” Confidence at its peak, Dean reached across the table for Cas’s hand and slipped it into his.

            In a strange twist – that Dean should have seen coming – Cas drew his hand back. His high swung low, and Dean slowly inched his way backwards.

            “Dean?” Cas asked, “What are – did you… _mean_ to do that?”

            Chuckling weakly, Dean answered. “Of course, Cas.”

            “…Why?”

            “Uh – well, s’what people do on _dates_.”

            Cas choked. “Date? This is a…” He ducked his head down, eyes frantically darting everywhere. “This is a date?”

            Dean wasn’t sure if the crack he heard was from a dropped plate or his heart shattering. “It was _supposed_ to be, yeah.” He couldn’t look at Cas, instead focusing his attention on the tablecloth he wrung in his grip.

            “Dean –“

            “It’s cool, Cas,” he forced a smile on his face, words wobbling on a tightrope of depression, “I should have – of course you’d… do you mind getting the check?”

            “Dean!”

            He rose quickly. “I’ll go get the car.” Dean fled from the restaurant, refusing to look behind at the very obvious scene he caused. His focus was more on preventing the full-bodied breakdown his mind was going through from causing him to drop into a fetal position.

            Dean was able to walk the two blocks towards Baby before things started shutting down. He leaned against her roof, breathing deep and blinking the tears back. Shuddering, he cursed at himself for thinking it was possible. “Of course,” he muttered, “You can’t have everything, Dean. Should’ve been happy with what you had…” Dean pounded a fist against his temple, still muttering to himself.

            Things would be awkward now. He’d have to explain to everyone how things went with Cas; dealing with their pitying glances and attempts to make him feel better. And worst of all, his and Cas’s relationship was ruined beyond repair. He wouldn’t be able to stand in the same room as him without his throat closing up and stomach upending on itself.

            It took forty years to finally come out of the closet, and in five seconds he was already trying to shove himself back in.

            So distracted, he didn’t hear Cas approach. A hand gripped Dean’s shoulder – _the_ shoulder. “Dean?”

            Steeling himself for the inevitable, Dean spun to face him. “Cas –“ he choked out, “I – I’m sorry –“

            “Don’t be!”

            Dean blinked at him. “W-what?”

            “You don’t have to apologize,” Cas told him, stepping closer, “I – I want this to be a date, too.”

            “I… I hit my head too hard, right?” Dean asked, “Because this, what you’re saying now, it’s not adding up to what happened back there.”

            Cas rolled his eyes. “What happened back there was _shock_. I didn’t know _you_ thought this was a date!”

            “Really?” he scoffed, “Because wasn’t it _me_ who asked _you_ to come here with me?”

            “Yes. Poorly.”

            “What?” Dean yelped, “No – no. I asked you out so _bravely_.” He psyched himself up in his bathroom mirror before searching for Cas. His angel was in the library, wrapped in a dusty tome. Clearing his throat, he caught Cas’s attention before it could read another yellowed page. And then, Dean asked if Cas would like to join him for an honest-to-goodness Valentine’s Day date because he liked him and wanted to be with him. After repeating all that to Cas, he said, “And you _smiled_ and _nodded_.”

            Cas huffed, dragging his hand down his face. “Dean, that’s now what happened _at all_.”

            “Come again?”

            “You nearly hacked up a lung,” Cas said, “And when I asked what was wrong, you deteriorated into a red-faced mess. You rambled out a string of words that were all tangled up. I only understood ‘pizza’, ‘together’, and ‘tonight’. I wanted to ask you more questions but you ran out of the room – much like you did just now.”

            “Well,” Dean said, “I think maybe we remember things a bit differently.” He scuffed his heel on the sidewalk, pocketing his hands. “You… you’re okay that this was a date?”

            Cas smiled then, dropping his other hand onto Dean’s untouched shoulder. “I’m _profoundly_ happy this was a date.”

            “O-okay,” Dean stuttered out, “I’m – um… I feel the same.” Then he _giggled_ , eyes most likely crinkling at the corners from how giddy he felt. His body shed thousands of pounds and would have floated up into the sky if not for Cas’s grounding touch. “You… you really didn’t think this was a date? On Valentine’s Day?”

            He hummed, closing the scant couple of inches that separated their chests. “Years of denying myself did wonders for my self-control. I couldn’t let myself hope that this would be anymore than dinner between friends.”

            “Yeah, well here’s the thing, Cas,” Dean said, “I don’t wanna be _just friends._ Haven’t for awhile.”

            “As have I, but… why now?”

            Dean smiled. “’M tired of keeping myself from the things I want. If I see it and I like it, then I go get it.”

            “…Are you quoting –“

            “Doesn’t matter,” he blushed, “What does is that I’m not holding back anymore. I’m running full throttle towards the things that make my life better, and Cas angel _you_ are my light at the end of that tunnel.”

            “That’s… kind of morbid, but also very sweet.”

            “Part of my charm.”

            “Please stop talking.”

            “There’s only one way to shut me up, angel.”

            “Then allow me…”

            Dean would never tell Cas this, out of fear that his angel won’t ever want to kiss him again if he knew, but when their lips met Dean felt transported to _Heaven._ His hands slid out from his pockets and glued themselves to Cas’s hips. Cas dragged Dean closer, wrapping his arms around Dean’s neck. They transitioned from a light peck to some heavy stuff, Cas making the first move with a swipe of his tongue. Dean opened up to him, leaning back against Baby as they kissed. His leg pressed up against Cas’s crotch. Dean smiled as he felt Cas’s excitement, even more so when he squeezed it and drew a gasp of pleasure from his angel.

            “Dean,” Cas breathed out, “do you think maybe we can take this… _nngh_ , somewhere else?”

            He chuckled, knocking his forehead up against Cas’s. “Sure thing. We can go home and… have dessert.”

            “Dessert?” Cas asked, “I thought you said you were full?”

            “What? No, Cas – I meant… _you know_.”

            “Oh… you’re talking about _sex_.”

            “Yes! But you don’t have to say it so loud…”

            “So you don’t want dessert, then?”

            “Why’re you asking?”

            “Because there happens to be a _pie_ waiting for you back home.”

            Dean opened his eyes, staring into the mirthful, blue sea of Cas’s loving gaze. “You serious?”

            Cas hummed. “I bought it the other day, to give to you tonight. I figured it was innocent enough the token could look friendly if not examined too closely… but now…”

            Dean beamed before planting a sloppy wet kiss on him. “Angel, if I didn’t love you already –“

            “You love me?”

            Dean wouldn’t miss a beat. “Of course I love you. Not like a brother, not like a friend – full blown romantic wouldn’t-want-anyone-else-but-you _love_.” He punctuated each word with a tiny peck on Cas’s face.

            Cas chuckled, pushing him away. “I really like this new you, Dean. You’re… _intoxicating_.”

            “Well I hope you’re ready to get _drunk_ on me tonight,” Dean joked, “Because I’m already feeling a little _tipsy_.”

            “Well then maybe _I_ should drive us home.”

            “Without a second thought,” Dean told him, “That’s how much I love you.”

            “If you keep this up we won’t make it home.”

            “Maybe that’s the plan?”

            “But then we’ll miss out on the pie.”

            “It’ll still be there no matter when we get back.”

            “But will it still be in the bedroom?”

            Dean paused, mouth dropping at Cas’s devilish smirk. “You mean…”

            “It’s been ten years Dean, I think you know me well enough I don’t beat around the bush… unless _asked_.”

            He opened the door for Cas, shuffling him in. “Well come on then! We don’t want to keep the pie waiting!”

            Cas held onto the door, laughing at Dean. He kissed him, soft and sweetly. “I love you, Dean. Knowing that we can have moments like this, well… it makes all the pining we did _worth_ it.”

            “And we’re gonna have so many more,” Dean said, “When we’re done, there’s not gonna be anything left _unspoken_ between us.”

            “Let’s get to it then.”

            Dean jogged to the other side, sliding into the driver’s seat. He put Baby in gear and peeled out of the spot. “Cas,” he said, “You wanna find something on the radio?” His angel flicked it on, only scouting for a few seconds before settling on a generic station.

            “This okay?”

            “ _Perfect_.”

            He held out his hand for Cas to take, which he did. Driving back to their home, Dean let his body go on autopilot. His mind instead focused on how right it felt being next to Cas, to _touch_ Cas. Their history was littered with missed opportunities, points where they could have taken their relationship one step further. But he didn’t look back with regret. Dean understood _why_ they never managed to get it right until now. There were still so many things they needed to go through, challenges to face, people to meet and lessons to learn. Like two lines drawing closer and closer, Dean and Cas finally converged and will continue on a single path – parallel no longer.

            And Dean would destroy whatever tried tearing them apart.


	5. Dean

            The pancake batter sizzled, its sweet aroma mixing with the savory smell of the bacon frying in the pan next to it. Cooling nearby was an already healthy stack of pancakes alongside deliciously fluffy eggs. Dean tied his robe tighter around him as a few drops of grease jumped out of the pan. He watched it all cook; posture loosened from the exhausting night he shared with Cas. Even though he was tired, he couldn’t force himself to stop smiling.

            Mary stepped into the kitchen then, yawning. “Someone seems happy to be up at this ungodly hour…”

            Dean shrugged. “ _Someone_ had to make you all breakfast.”

            “I could’ve made breakfast.”

            “Sorry,” Dean said, “I meant someone had to make you all _edible_ breakfast.”

            She huffed, shuffling over to the table. “If I wasn’t so tired I’d cuff you for your smart mouth.” As he finished with the last pancake, Mary called to him. “So… how’d your date go last night?” she asked.

            “As good as you’d expect,” he shrugged, “except _better_.”

            “So you and Cas…”

            Dean turned to her and nodded, shyly ducking his head.

            Mary clapped, “Fantastic! I want to hear _everything_.”

            He blushed, spinning back around to his cooking. “Everything, Ma? You sure?”

            “Not _everything_ -everything,” she scoffed, “Unless you want _me_ to talk about my date with Bobby? Because _then_ I can go into everything-everything detail.”

            Dean gagged. “Seriously, keep this up and you’re out of bacon.”

            “We’re out of bacon?” Sam stepped into the room, then. His hair was a mess, and his clothes were rumpled and clearly the same he wore last night.

            Dean raised a brow at him, crossing his arms. “Did _someone_ just get back from their date?” Instead of answering, Sam crossed over into Dean’s space to grab a few strips of bacon from the plate. “Hey!” Dean cried, swatting him with the spatula, “Back off!”

            “Sorry, Dean,” he said, chomping down on three strips, “I’ve got major munchies.”

            Snorting down a huge whiff of Sam, he knew why. “Go get some coffee,” he whispered, “try and sober up at least.”

            “…What?”

            “Man you really went native with that hippie chick didn’t you?”

            Sam chuckled. “Dude, after the poetry thing we went back to her place and she made _smoothie_ _bowls_. And then…”

            “Fill me in later when you’re not stoned,” Dean said, clapping him on the arm, “Why don’t you go and take a seat. _Then_ you can dig in.”

            “Cool…”

            Like a revolving door, once Sam was seated the next person made their way in. Jack floated through the entryway, like Dean and Mary still in his pajamas. “Morning everyone!” They responded in kind, Sam’s very delayed due to a fascination with the salt and peppershakers. He bounced over to Dean, “You’ll never guess what happened to me last night.”

            “What?”

            “I had my first kiss!”

            Dean laughed, “Really?”

            Jack nodded, beaming like a spotlight. “We were playing this game called Seven Minutes in Heaven. I was confused at first because humans couldn’t enter Heaven without being dead, and I warned Eliot of this fact. But then he explained it to me and when they spun the bottle it landed on us so we went in the closet and –“

            “I know what happens next kid,” Dean stopped him, “Not my first rodeo. You can finish your story while we’re chowing down.” He shooed him away, telling him to set the table. It wasn’t long before the last of his bacon was fried to a crisp. “Okay,” he said, “I hope you’re all ready!”

            Dean carried the food over, making two trips and adding an extra one to grab the orange juice from out of the fridge. Sitting down next to Sam, he moved to spear some bacon only for Mary to stop him.

            “Aren’t we waiting for someone?”

            Dean snorted. “I figured Bobby would’ve come in with you.”

            “He's still sleeping,” she said, “I mean, where’s Castiel?”

            “I sent him out to run an errand for me.”

            “Shouldn’t we wait for him?”

            “It’s not like he’s missing out.” Dean glanced at the entrance. “Although, I did send him out a while ago… shouldn’t have taken this long.”

            Sam chuckled, dumping tons of syrup onto his pancakes. “D’you think maybe something grabbed him? Made him disappear?”

            Jack, a forkful of eggs in hand, froze with them halfway to his mouth. His eyes widened as his grip slackened. Dean skewed his head to the side, more curious with Jack than annoyed with Sam. He almost asked what was wrong, but then Cas swept in with a black plastic bag. All questions flew from his mind when he laid eyes on his angel.

            “Hey, Cas,” he said, “What took you so long?”

            “There was a long line,” he told them, pulling a pie out from the bag, “Apparently February 15th is a busy day…”

            Mary balked at his purchase. “Pie? For breakfast?”

            Dean snatched it out of Cas’s hands. “It’s to celebrate.”

            “Celebrate what?”

            “Love,” he said, raising the tin in mock toast. “Family… being together. If it’s cheesy than we’re definitely celebrating.”

            Sam frowned at the pie. “There’s cheese in that pie?”

            “…Focus on your pancakes, Sam.”

            Cas carried over a knife, handing it to Dean before taking his place next to him. Draping his arm over his shoulder, Cas kept it there throughout all of breakfast.

            Their little family enjoyed the morning together, laughing and sharing stories. It got a little misty-eyed when Dean openly kissed Cas after feeding him a bite of pie. Mary was to blame, her leaking tears provoking Dean to shed a few of his own.

            Sam, on the opposite end of the emotional spectrum, huffed a laugh at Dean’s feeding scene. “Dude, that’s so gay.”

            Dean fired back with, “Yeah, well _I’m_ gay Sammy.”

            “Cool.”

            It was one of the best breakfasts Dean ever had. The atmosphere was lighter than he could ever remember, and even the taste of bacon mixed with pie was incomparable to the good feelings he sensed from all around. And in that moment, Dean only had one person in mind he could thank, as shocking as it might seem.

            John Winchester was a shell of a man after Mary died, and should not have been left to his own devices when concerning his two young children. Because of this, Dean had a hell of a life. He had been through the wringer more times than he can count, and was scorched by both real and metaphorical flames. His childhood was a ratty tapestry stitched together of far-flung moments and escapist fantasies. And as an adult he spent more years recovering from traumas most people are lucky enough to never see a fraction of.

            Yet he’s still here. So he thanks his dad, because if he never had to crawl through all the shit he left them, Dean never would have been able to savor the sweet air of freedom once he made it out the other side.

**Author's Note:**

> You like? Let me know! Drop a kudos/comment down below!! They're what keep me going on days like this where it's even more glaringly obvious that I'm going to die aloooone.


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